N,N-Dimethyl-1,3-propanediamine → HCID 9908413, compound

HRID 1634137Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6]([C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=O)=[CH:5]2.CCN=C=[N:25][CH2:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30].C1C=NC2N(O)N=NC=2C=1.CN(CCCN)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6]([C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([NH:25][CH2:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])=[O:16])=[CH:5]2

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of crude 2-(5,6-dichloro-1H-indol-2-yl)benzoic acid (0.19 g, 0.62 mmol), WSC (0.13 g, 0.68 mmol), HOAT (0.093 g, 0.68 mmol), dimethylamino propylamine (0.13 g, 1.3 mmol) in DMF (2 ml) was heated at 50° C. for 16 h. The mixture was then poured on water and extracted with ethyl acetate. The organic phase was washed twice with water, dried over MgSO4, concentrated in vacuo and the residue was purified by column chromatography (SiO2, CH2Cl2/CH3OH/NH4OH; 9/1/0.1) to afford the title compound as an oil, which crystallised by trituration in diisopropyl ether obtaining, after filtration, 0.072 g (0.18 mmol yield 30%) of the title compound as white crystals, mp=169° C.

Workup

additionThe mixture was then poured on water
extractionextracted with ethyl acetate
washThe organic phase was washed twice with water
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customthe residue was purified by column chromatography (SiO2, CH2Cl2/CH3OH/NH4OH; 9/1/0.1)

Sources & evidence

ORD record: ord-271ddac2545e419ca5607dc72073b5f1
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06506758B2

Reaction notes

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